Recently, Alex and I had one of the best conversations about Path 101 that we've had with an investor so far. We talked about what we've learned, the space, our approach, etc. They were extremely thoughtful in terms of where the market is going and how to best take advantage of the opportunity. We riffed for nearly two hours.

A day or two later, I was talking with a successful startup guy who was going to make a key introduction for us. I had been nearly tripping over myself in terms of all the potential for value creation we had and the opportunities missed by others. (I get pretty passionate about this stuff.) I then asked him about how "pitchy" I should be when talking to this potential new investor.

"The last ten minutes of our conversation--that's what you need to have with him," he said.

That's when I realized how inauthentic and contrived the whole pitch process was. You'd never find your soulmate, make a friend, or hire someone based on a Powerpoint--so why find someone to invest in your company that way? Either show your product or just talk to the person--with the latter probably being much more effective in presenting a vision and as a way to get to know you as a person.

The other thing about a "pitch" is that the tone of the conversation is negative. Investors are looking for holes--reasons not to invest, because the default is a no. Conversations don't have a default answer that you have to hurdle over, they're just an exchange.

I don't think enough entrepreneurs get out from behind their desks to talk to the market--to business development partners, to investors, to prospective employees... to anyone who could give useful product feedback. I can't tell you how many times I've talked to startups and said, "Oh, you know so and so, right?" They rarely do... even when it's a no-brainer that they should be talking to a completely obvious partner or investor.